Ethyl propiolate → HCID 89650589, compound

Participants

Reaction Steps

To a solution of Compound 132 (50 mg, 0.11 mmol) in DMF (1.8 mL) was added ethyl prop-2-ynoate (21 mg, 0.2218 mmol), followed by ethyl-diiopropylamine (0.023 mL, 0.13 mmol) and cuprous iodide (3.8 mg, 0.020 mmol) at 0° C. The ice bath was removed and the mixture stirred at RT for 2 hours. Water was added and the mixture extracted with EtOAc (4 times). The organic fractions were combined and concentrated in vacuo to give a residue that was purified by medium pressure chromatography (C18 column), eluting with ACN gradient in water, to give target product. The product was triturated with EtOAc to give Compound 133 (5 mg). 1H NMR (400 MHz, DMSO) δ 10.55 (s, 1H), 9.82 (5, 1H), 9.43 (s, 1H), 9.12 (s, 1H), 8.62 (s, 1H), 7.94 (t, J=6.4 Hz, 5H), 7.44 (d, J=8.5 Hz, 2H), 7.31 (d, J=8.5 Hz, 2H), 7.26 (s, 1H), 4.37 (q, J=7.1 Hz, 2H), 3.20-3.11 (m, 2H), 1.35 (t, J=7.1 Hz, 3H), 1.07 (t, J=7.2 Hz, 3H), [M+H]+ m/z=549.03.

Provenance & Evidence